Uncovered in San Francisco

Note : my other stories attracted the attention of a reader, who shared with me one of her fantasies, and wished to see it made alive. So this one is for Anne.

*

San Francisco, September 2022. I was back here for the first time in more than a decade. A young (relatively speaking) retiree since a little while, I had agreed to come give a hand to a friend with whom I had been in business in the past, and who was in the process of selling his tech startup to a company based here in the Bay Area. One of the Sand Hill Road venture capital groups was financing the transaction, I had had a good relationship with them in the past, I went to visit them to provide some background info. Everything had gone swimmingly, we had a verbal agreement, now the deal was in the hands of the lawyers and accountants.

Besides the fact that I stood to receive a few hundred thousands in the deal, being one of the early stage investors in my friend's startup, I was feeling good about my day. My last stay here had been with my ex, shortly before we separated, but I kept good memories of this city which I had been visiting regularly for more than thirty years. The only less cheerful part was the prospect of yet another evening dining alone in a hotel restaurant, before flying back home to Montreal tomorrow. Just one phone call to make to my friends at their office in Montreal to give them the last update, which I had started on while walking the short distance from the corner of Market Street, where I had asked the Uber to drop me off, given the heavy traffic, to the Marriott Marquis. I was finishing up my verbal account, in French, as I walked into the elevator just as the doors were closing.

"Yeah, Vivek had some concerns about the holdback amount for the intellectual property issues. I cleared them up, no more worries on his part. I have to go, I'm getting into the elevator. Bye."

It was then that I noticed that there was already someone in the elevator, a woman, who seemed puzzled by what I had just said in French. "Sorry," I said in English. "It's very impolite of me to be on the phone in an elevator. My apologies." Spoken like a true Canadian.

She answered me with a pretty shy smile, and also in French: "No reason to apologize. It sounded important." She was my age or thereabouts, late fifties or perhaps older, but in great shape, wearing a shortish and elegant skirt, pretty stockings on shapely legs, very cute ankle boots in soft leather, a tailored jacket that was buttoned up but hinted at beautifully round breasts, a silk scarf around the neck. Very posh, I thought. A late stage MILF, would that be a GILF?

"It was indeed, but I'm done, I won't be bothering you anymore."

"You're not bothering me at all," she laughed. "I wasn't expecting to hear someone speaking French, that's all. I gather you're not here as a tourist?"

"No, I'm here on business, but I always enjoy being in this town, which I have loved for a long while. And yourself?"

"Me, as a tourist, but it's my first time. I don't know it at all," she answered still with a nice smile, blushing slightly.

She had something very attractive about her, I have always liked when women of a certain age -- heck, my age -- had a way of showing a still sexy side. The elevator was reaching my floor. I then said:

"I'll be going up to the hotel bar in a few minutes after dropping off my things, if you like I can point out interesting sights for you to see during your stay."

I am not at all any kind of pick-up artist, and I was afraid she might take it that way, but I was sincere. I was in a good mood, I wanted to share my enthusiasm for this town, and she seemed nice. The sexy vibe which emanated from her had burned right through my usual reserve.

"Ah... maybe... I don't know..." she answered, slightly flustered but still smiling.

"Well later then, or if not have a great stay!" I said as I stepped out.

About twenty minutes later, I was sitting down sipping the last of a Negroni at the View Lounge, the fancy bar at the top of the hotel, with a fantastically huge floor to ceiling bay window in Art Deco style offering a breathtaking view of San Francisco Bay, the light of the golden hour reflecting off the glass facades of neighbouring high rises. And I saw her arriving, looking like she was searching for me, then seemingly reassured to find me and heading for my table. Really really nice, great smile, bright eyes behind her glasses, a nice sway to her hips in her tight skirt. The tailored jacket was gone, confirming the roundness of the aforementioned tits, even if they were covered by the scarf and the buttoned-up blouse. I stood to advance one of the stools bordering the table and inviting her to join me. As she sat down, her tight skirt rose up a little, showing a brief flash of thigh above what I guessed to be hold-up stockings. Chic and sexy, I thought. She had a bit of an awkward smile and blushed again, trying to pull the hem of her skirt back down. Which was a bit difficult given the height of the stool and the tightness of the skirt.

"It's really magnificent here. I'm a bit uneasy, I have the impression that everybody can see my legs."

"Seated as you are on the edge of a glass wall on the thirty-ninth floor, in that direction you are bringing joy to about four hundred and fifty thousand people." I answered with a smile. She blushed even more. "but that's the risk you take wearing a pretty skirt like that. Life is good." I concluded. She seemed very uneasy but happy of the compliment.

She told me she had arrived from France the day before with a friend, but a combination of jet lag and some kind of flu bug caught in the plane had knackered her friend, who told her that she wanted to sleep it off in her room. Her English skills were poor, not a surprise for me from a French citizen. It was her first time in California. I recommended a local sparkling wine, and ordered one for myself to keep her company.

The conversation flowed easily. I told her about places I enjoyed here, the ruins of Sutro Baths with the Cliff House restaurant, Coit Tower, Haight-Ashbury, the bison in Golden Gate Park, the ferry to Sausalito, Marin Headlands with the view of the bridge. We talked a bit about our lives, she told me her name was Anne, that she had been living alone for a while, that she was in a relationship with an older man who was a bit of a homebody. This trip she had organized with her friend spring from a desire for change and renewal. She told me she wanted to use the opportunity of this trip to spruce up her outfits, which she had not done in a while. Great idea, I said, just next to here there is the Westfield shopping center with lots of shops, all the international chains but also more local and original brands she would not find in France. What was she looking for exactly? She wanted a bit of change, she thought she has been wearing the same kind of thing for ever, she was a bit tired of being seen as a posh but prim and proper lady. I told her that hold-up stockings are not really so prim and proper, she found that funny. I offered to accompany her for her shopping. Really? You would? Why not, I said. I enjoy your company, I have nothing better to do, I'm happy to help you become less proper...

My intuition was that her desire for renewal went beyond her wardrobe. She gave me the impression of a woman who wants to test if her power of attraction still works, the passing years leading her to start having doubts. In my opinion it still worked in a major way, but I felt that to just tell her that, here and now, would be to miss an opportunity. There was something else.

Walking towards the Westfield center, across the street. Same unavoidable international brands you can find on the Moon, but I point out to her Bloomingdale's, Nordstrom, which are more typically American. She's a bit disappointed to find that the clothes on display are not that different from those she is already wearing. Agreed, a tailored jacket and skirt, however nicely short, remains a tailored jacket and skirt. Let us blaze a new trail.

"Your eyes naturally turn to prim and proper stuff out of habit. I think you should go further in the same direction."

"Further in the same direction? What do you mean?"

"You're wearing a skirt suit. It's chic, and sexier than pants. This skirt is relatively short compared to what most women your age wear. It causes you to sometimes, inadvertently, show the top of your thighs. Most women would wear pantyhose with that, it's modern and practical. You choose to wear thigh-high stockings, even though there is a risk that your short skirt causes you to flash your thighs. I think that unconsciously, or not so much, you like your thighs to be seen. Am I wrong?"

Same crimson color as earlier. I've hit the bullseye. There is a crack in all things, that's how the light gets in, sings Leonard Cohen. The crack now being lit, we shall enter.

"It excites you. But you don't want to admit it to yourself. Earlier when I told you that four hundred thousand and fifty people could see your legs, you flushed with pleasure. Even though in practice, no one actually saw anything. That's the direction you want to take." And that I want you to take as well, I thought.

She mumbles, says I'm exaggerating, that I misunderstand. But she is not being sincere and you can hear it. I drag her by the hand to the second level. Another boutique, called Bebe. On the mannikins, short skirts and dresses, buttons and zippers everywhere. Stretchy shiny fabrics, glitter, leather.

"But those are clothes for young girls who are going out clubbing," she protests.

"No. They are clothes for women who are sexy and wish it to be known. It says so in great big letters at the entrance: An Attitude, not an Age. Age doesn't have as much to do with it as muscle tone. Tina Turner was wearing spectacular miniskirts past age 70. We'll find outfits for you to try."

Before she can turn around to leave, I speak to the miniskirted pretty young thing with neverending legs who is standing close to us but has been hesitant to interrupt our conversation in French.

"My friend says she is looking for a skirt that's at least as sexy as the one you're wearing. She told me not to translate that because she's a little shy." I tell her with a wink. Gotcha, her eyes say. She picked up on the group dynamics immediately. Smart girl.

"Absolutely! We've got great new arrivals that will turn her on, and you! Let me get a few."

She brings us a few selections from the displays. My personal choice has settled on a mid-thigh length A-line skirt, pleated, in a fine leather-like material, with a zippered closure on the side. The leather has a lustrous sheen which will catch the light and the eye. The way it drapes with the pleats leads us to believe that the skirt will swish marvellously to and fro with every movement. The density of the fabric ensures that said movements will be conserved by the force of inertia. Yet, the lightness is sufficient to allows us to anticipate that, given the average wind speed in this region of Northern California, some of these movements will be random and thus, plausibly unvoluntary. The thoughtful man considers these things. In Chicago, for instance, this skirt would immediately turn horizontal as if hung from a flagpole. Which wouldn't be, in itself, a bad thing. But not the subtle effect we are looking for.

Anne goes to try on the skirts in a changing booth, but I've already chosen. While she is away, I ask the salesgirl to bring us a selection of light and sheer tops. She is amused and rushes off enthusiastically to fulfill the request.

Anne returns after a little while, she has tried on the skirts. She finds them a little bit short for her liking, but does admit that she likes the way she looks in them:

"Thank you for pushing me into trying that, I don't believe I would have done so by myself. I don't know when I would have the occasion to wear something that short, though."

The salesgirl is back with a selection of blouses, tops, silk t-shirts, etc. While Anne is busy looking at what she brought, I ask the salesgirl in a low voice:

"She loves the leather skirt but she says it's one size too long. Can you bring her the same waist size, but shorter?"

It's her turn to wink at me as she goes to get the skirt. I send Anne back to the changing room with the tops. As she is on her way, the girl comes back with the other skirt. I bring it to Anne and tell her to try it on again so we can see the look with the tops.

She shily steps out to show us the result. It's boner inducing. The skirt barely manages to cover the top of her stockings. The pearl grey top only has four buttons, which are done up all the way. It is made of a very sheer and extensible fabric which hugs her shoulders, back, arms and breasts. Her black bra is clearly visible under it, with beautiful openwork lace patterns. Even the salesgirl is speechless, she is biting her lower lip and fidgeting.

"I can't go out like this," she protests. "Everyone will see my bra."

"We're just following through on the hold-up stocking concept. What's the point of a pretty bra if it's to hide it?"

The life unexamined is not worth living, teaches Socrates.

"But if it really worries you, we can add a cute little leather jacket over it. Which will put the nail in the coffin of the prim and proper look."

Which the salesgirl provides us with posthaste, a tiny thing with lots of zippers. This being California, she assures us that the leather is vegan, that the zippers contain no Russian steel and the whole thing was put together in carbon neutral factories that do not involve forced labor by underage lab animals.

While Anne is still hesitating, looking at her reflection from all sides in the mirror with the jacket on, I tell the salesgirl in a low voice that we will take the outfit, and that she can wrap Anne's own clothes which are still in the changing booth, for delivery in her name at the Marriott concierge desk.

I pay discreetly while Anne is turning around over and over nervously before the mirror, still not convinced. I take her hand and drag her towards the exit. She protests, nervously:

"But my clothes?"

"They will be waiting for you tonight at the Marriott. We're not done shopping."

She has just realized that the skirt is shorter than expected, and that the edge of the lace bands is peeking out with each step. On top of that, it almost seems like gravity is being temporarily reduced around the skirt, which swishes insolently. I walk fast, pulling her along by the hand. Her eyes are damp, her face a shows a kind of awkward confusion. She would protest but only manages a few incoherent mewing sounds.

Second stop, Victoria's Secret. Tame, not so tame, and not tame at all lingerie. I show her the Bluebella collection, in which among other things we find a set of minimalist panties that consist of effectively no fabric at the back, and a mere hint of a triangle at the lower front, which is completely transparent. The matching bra is in the same theme: other than the shoulder straps and a thin strip of black fabric below the breasts, in lieu of the cups there are only five thin gold chains. She says no, it's out of the question, she won't even try it on. I ask a salesgirl to bring a set in Anne's approximate size. With so little fabric involved, precise fitment should not be much of an issue.

"Even if you don't want to try them on, let's take them. You might change your mind someday."

She seems confused, ashamed, and happy all at once, as the salesgirl spreads out the set on her countertop to fold and wrap it, under the amused glance of a few clients. Anne's short skirt and the bits of sheer blouse that can be hinted at under the jacket are attracting the attention of men and women alike. Anne is blushing again, as I put the tiny package in my jacket pocket.

We leave the building heading towards Market Street, night has fallen. Anne notices that this is not the street adjoining the hotel. I tell her:

"Since we don't have any packages to drop off, why go back to the hotel? Let's go for dinner in North Beach, lots of great restaurants there. And then we'll go out. It would be a shame not to show off the bold new you right away, I'm sure you're anxious to do so."

She would protest but cannot manage to speak. Then gradually her worried expression turns into a slight smile, and she suddenly squeezes my hand very hard. This is a resounding yes that she can't verbalize.

We cross Market street at the intersection of Powell, where there is one of the end of the line stations of the famous San Francisco cable cars. These are century old tramways that are powered by a cable that runs continuously in a groove in the street. The rails are at pavement level and ordinary cars share the roadway with the trams. The operator only has to actuate a clutch that clamps and releases the cable, or to use the brake in the hills. And San Francisco has no lack of hills. It's still a functional mode of transportation, although mostly used by tourists. One of the cable cars is about to leave, it's already packed, I climb on the rear platform, dragging Anne by the hand, and we hang onto the ceiling bar. We are right on the edge of the platform, and thus Anne's ass is slightly above the level of the windows of nearby cars. I am diabolical.

The tram starts uphill on Powell street. The jerkiness of the motion, the sudden change of angle when crossing intersections, and the gusty breeze, all combine marvellously to make Anne's short skirt dance. We are no longer talking about vague hints of the edge of a garter: Anne is showing to the passerby the whole extent of her bare thighs all the way to the swell of her buttocks, which are still covered by pretty black panties. But the night is still young.

The folk in the following car have their eyes on the prize. I can see the head of a rear-seat passenger bent forward between the seats to have a better view. Another car that's moving alongside in the other lane has slowed down to keep pace with us. This seems to exasperate the driver of the following vehicle, one of these ridiculously large SUVs, who from his higher seating position is missing the show. Serves him right for destroying the planet.

A few minutes later, the tram rails turn West on Jackson, then North again on Mason. We get off at Green avenue. During all the ride, Anne has kept her eyes to the ground, red with shame, one hand holding the bar. But her other hand has not left mine and is still squeezing hard.

We walk up the hill on Green. We are in North Beach, once a neighborhood of Italian immigrants now as gentrified as the rest of the city. There remains some excellent restaurants that have fused their Italian traditions with modern techniques and tastes, so very Californian. I take Anne to one were I have been before. We have no reservations, but it's a weekday evening, the ground floor room is maybe two-thirds full. But when the Maître d' suggests a table downstairs near the bar, I ask if we can rather have one on the upper mezzanine that overhangs half of the room. An L-shaped stairway leads to it, one part of the stairs above the middle level landing adjoining the side edge of the mezzanine. He brings us to the table that stands on the corner of the stairway at the front of the mezzanine. I pull back a chair for Anne to sit facing the ground floor, on the stairway side. All the railings of the mezzanine and stairway are plate glass. How lovely.

Anne has sat down pulling her skirt under her legs, and looks down at the room a bit nervously. After the menus have arrived, I tell her:

"You should pull the back of your skirt out from under your legs, you will make creases in the leather pleats. Which would be too bad."

She freezes, puts her menu down. I take her shaking hand and squeeze it in turn. After a moment's hesitation, she lets go of my hand, then reaches to her waist, lifts up a little in her chair, and pulls her skirt out from under her legs toward the seat back. She smooths the front of her skirt over her legs. The skirt is long enough to easily cover the top of her stockings, but with the pleats it drapes nicely at the sides, revealing the lace trim and a good part of her thighs diagonally until it meets the seat cushion.